US11638950B2 - Articles prepared using curable compositions based on polymerizable ionic species - Google Patents
Articles prepared using curable compositions based on polymerizable ionic species Download PDFInfo
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- US11638950B2 US11638950B2 US17/258,558 US201917258558A US11638950B2 US 11638950 B2 US11638950 B2 US 11638950B2 US 201917258558 A US201917258558 A US 201917258558A US 11638950 B2 US11638950 B2 US 11638950B2
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- Prior art keywords
- meth
- curable composition
- functional group
- polymerizable
- cured
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- 239000000203 mixture Substances 0.000 title claims abstract description 289
- 125000000524 functional group Chemical group 0.000 claims abstract description 94
- 238000000034 method Methods 0.000 claims abstract description 86
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- 125000000129 anionic group Chemical group 0.000 claims abstract description 52
- 125000002091 cationic group Chemical group 0.000 claims abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 84
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- -1 allylsulfonate Chemical compound 0.000 claims description 44
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- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 8
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
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- YQSVYZPYIXAYND-UHFFFAOYSA-N 2-(prop-2-enoylamino)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(CC)NC(=O)C=C YQSVYZPYIXAYND-UHFFFAOYSA-N 0.000 claims description 4
- DMSRIHVZKOZKRV-UHFFFAOYSA-N 2-methyl-1-(2-methylprop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C(C)=C DMSRIHVZKOZKRV-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
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- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical group [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 4
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
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- ZTWTYVWXUKTLCP-UHFFFAOYSA-L ethenyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-L 0.000 claims description 2
- NZRFSLMXTFGVGZ-UHFFFAOYSA-N n-[diethylamino(prop-2-enoxy)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)OCC=C NZRFSLMXTFGVGZ-UHFFFAOYSA-N 0.000 claims description 2
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- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 6
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 6
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
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- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 4
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- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- RZKYDQNMAUSEDZ-UHFFFAOYSA-N prop-2-enylphosphonic acid Chemical compound OP(O)(=O)CC=C RZKYDQNMAUSEDZ-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002520 smart material Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- SGKKYCDALBXNCG-UHFFFAOYSA-N tris[2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-5-methylphenyl] phosphite Chemical compound CC(C)(C)C1=C(O)C(C)=CC(SC=2C(=CC(OP(OC=3C(=CC(SC=4C=C(C(O)=C(C)C=4)C(C)(C)C)=C(C)C=3)C(C)(C)C)OC=3C(=CC(SC=4C=C(C(O)=C(C)C=4)C(C)(C)C)=C(C)C=3)C(C)(C)C)=C(C=2)C(C)(C)C)C)=C1 SGKKYCDALBXNCG-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
- B22C1/16—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents
- B22C1/20—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents
- B22C1/22—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins
- B22C1/2206—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B22C7/00—Patterns; Manufacture thereof so far as not provided for in other classes
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- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
- B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
- B29C64/129—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/20—Apparatus for additive manufacturing; Details thereof or accessories therefor
- B29C64/245—Platforms or substrates
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y10/00—Processes of additive manufacturing
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
- C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
- C08F271/02—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00 on to polymers of monomers containing heterocyclic nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
Definitions
- the protic liquid medium is substantially neutral (pH 6-8). Water having a pH of 6 to 8 is used as the protic liquid medium in certain aspects of the invention. However, in other embodiments the protic liquid medium is acidic (pH less than 6) or basic (pH greater than 8). The pH of the protic liquid medium may be adjusted using inorganic and/or inorganic acids, bases or buffering agents.
- the protic liquid medium may have one or more solutes dissolved in it; for example, the protic liquid may contain one or more dissolved salts, such as sodium chloride.
- the ethylenically unsaturated group present in the anionic species may be the same as, or different from, the ethylenically unsaturated group present in the cationic species.
- the curable compositions employed in the present invention may comprise one, two, three or more polymerizable ionic species.
- the term “polymerizable” means a substance, species, compound, moiety or functional group capable of combining by covalent bonding in an addition polymerization. According to certain embodiments, such a polymerizable substance, species, compound, moiety or functional group is capable of being polymerized by a free radical mechanism (“free-radically polymerizable”). According to other embodiments, the polymerizable substance, species, compound moiety or functional group is actinically polymerizable (i.e., capable of being polymerized by exposure to actinic radiation, such as UV or visible light).
- the carbon-carbon double bond may, for example, be present as part of an ⁇ , ⁇ -unsaturated carbonyl moiety, e.g., an ⁇ , ⁇ -unsaturated ester moiety such as an acrylate functional group (H 2 C ⁇ CH—C( ⁇ O)O—) or a methacrylate functional group (H 2 C ⁇ C(CH 3 )—C( ⁇ O)O—).
- an acrylate functional group H 2 C ⁇ CH—C( ⁇ O)O—
- methacrylate functional group H 2 C ⁇ C(CH 3 )—C( ⁇ O)O—
- the protonated amino group may be a protonated primary amino group —NH 3 + , a protonated secondary amino group —NRH 2 + wherein R is an organic moiety such as an alkyl group, or a protonated tertiary amino group —NR 1 R 2 H + where R 1 and R 2 are the same or different and are organic moieties such as alkyl groups) or a protonated amido group —C( ⁇ O)NR 3 R 4 H + (where R 3 and R 4 are the same or different and are selected from the group consisting of hydrogen and organic moieties, such as alkyl).
- the precursor to the polymerizable cationic species may have a pKa of 3 to 16.
- the precursor to the polymerizable anionic species may have a pKa of ⁇ 10 to 10.
- the curable composition may be comprised of not more than 50 percent by weight, not more than 40 percent by weight or not more than 30 percent by weight of one or more curable compounds which are not polymerizable ionic species in accordance with Formula (I).
- the optionally present additional curable compounds may be, for example, polymerizable ionic species not in accordance with Formula (I) and/or non-ionic polymerizable compounds.
- Such compounds may act as covalent crosslinking agents, thereby interfering with the ability to readily fragment, using a protic liquid medium, an article obtained by curing the curable composition.
- the curable composition is comprised of less than 5, less than 4, less than 3, less than 2, less than 1 or less than 0.5 percent by weight in total of compounds having two or more covalently-linked polymerizable ethylenically unsaturated functional groups per molecule.
- the carbon-carbon double bond may be present as part of an ⁇ , ⁇ -unsaturated carbonyl moiety, e.g., an ⁇ , ⁇ -unsaturated ester moiety such as an acrylate functional group or a methacrylate functional group or an ⁇ , ⁇ -unsaturated amide moiety such as an acrylamide functional group or a methacrylamide functional group.
- a carbon-carbon double bond may also be present in the additional ethylenically unsaturated compound in the form of a vinyl group —CH ⁇ CH 2 (such as an allyl group, —CH 2 —CH ⁇ CH 2 ).
- the amount of light blocker may be varied as may be desired or appropriate for particular applications. Generally speaking, if the curable composition contains light blocker, it is present in a concentration of from 0.001 to 10% by weight based on the total weight of the curable composition.
- the curable composition may contain one or more solvents, in particular one or more organic solvents, which may be non-reactive organic solvents.
- the solvent(s) may be relatively volatile, e.g., solvents having a boiling point at atmospheric pressure of not more than 150° C. In other embodiments, the solvent(s) may have a boiling point at atmospheric pressure of at least 40° C.
- the curable compositions of the present invention may optionally contain one or more additives instead of or in addition to the above-mentioned ingredients.
- additives include, but are not limited to, indicators, photostabilizers, foam inhibitors, flow or leveling agents, buffering agents, dyes, colorants, pigments, dispersants (wetting agents, surfactants), slip additives, fillers, chain transfer agents, thixotropic agents, viscosity modifiers, matting agents, impact modifiers, waxes or other various additives, including any of the additives conventionally utilized in the coating, sealant, adhesive, molding, 3D printing or ink arts.
- the curable compositions of the present invention are also characterized by containing little or no water and (meth)acrylic anhydride.
- the curable composition may, for example, comprise less than less than 10,000 ppm, less than 9000 ppm, less than 8000 ppm, less than 7000 ppm, less than 6000 ppm, less than 5000 ppm, less than 4000 ppm, less than 3000 ppm, less than 2000 ppm, less than 1000 ppm, less than 500 ppm, less than 100 ppm or even (most preferably) 0 ppm (meth)acrylic anhydride.
- the sacrificial material (support) formed from the curable composition of the present invention may be removed or otherwise separated from the article using a protic liquid medium (with the 3D-printed article being constructed of a material which resists fragmentation by the protic liquid medium).
- An article made by printing, in a three-dimensional manner, a curable composition comprising of at least one polymerizable ionic species corresponding to Formula (I): A + B ⁇ (I) wherein A + is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B ⁇ is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group, as described elsewhere herein in more detail, may be substituted for a conventional wax or plastic pattern in such an investment casting process.
- a method of making a three-dimensional article comprising printing the three-dimensional article using a curable composition comprised of at least one polymerizable ionic species corresponding to Formula (I): A + B ⁇ (I) wherein A + is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B ⁇ is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group;
- Aspect 2 The method of Aspect 1, wherein the curable composition when cured provides a cured composition having a hardness greater than 20 on a Durometer 00 scale or greater than 0 on an A and D scale.
- Aspect 12 The method of any of Aspects 1 to 11, wherein the curable composition additionally comprises at least one additive selected from the group consisting of photoinitiators, antioxidants, and light blockers.
- Example 1 is repeated using the following components: 2-acrylamido-2-methylpropane sulfonic acid (30 g), N-[3-(dimethylamino)propyl]methacrylamide (70 g), and Irgacure® 4265 antioxidant (2 g).
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- Polymers & Plastics (AREA)
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- Medicinal Chemistry (AREA)
- Manufacturing & Machinery (AREA)
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- Optics & Photonics (AREA)
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- Dental Preparations (AREA)
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Abstract
Description
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group;
wherein (in at least certain embodiments) the curable composition does not comprise significant amounts of (meth)acrylic anhydride or water and wherein the curable composition when cured provides a cured composition which displays thermoplastic behavior in the absence of a protic liquid medium, is fragmentable in a protic liquid medium and comprises ionic crosslinks as a result of incorporation of the ionic species into a polymeric matrix.
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group. In one embodiment, the cationic species comprises a single cationic functional group. In another embodiment, the cationic species comprises a single polymerizable, ethylenically unsaturated functional group. In a further embodiment, the anionic species comprises a single anionic functional group. According to yet another embodiment, the anionic species comprises a single polymerizable, ethylenically unsaturated functional group.
- i) cyclic monofunctional (meth)acrylate monomers, such as isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, 4-tert-butyl cyclohexyl (meth)acrylate and alkoxylated analogues thereof; and
- ii) linear and branched mono functional (meth)acrylate monomers, such as isodecyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, polyethylene mono (meth)acrylates, neopentyl glycol (meth)acrylates and alkoxylated analogues thereof, as well as caprolactone-based (meth)acrylates prepared by addition of one, two, three or more moles of caprolactone to a hydroxyalkyl (meth)acrylate such as hydroxyethyl (meth)acrylate (“caprolactone adducts of hydroxyalkyl (meth)acrylates”).
- a) coating a first layer of a curable composition in accordance with the present invention onto a surface;
- b) curing the first layer, at least partially, to provide a cured first layer;
- c) coating a second layer of the curable composition onto the cured first layer;
- d) curing the second layer, at least partially, to provide a cured second layer adhered to the cured first layer; and
- e) repeating steps c) and d) a desired number of times to build up the three-dimensional article.
- a) coating a first layer of a curable composition in accordance with the present invention and in liquid form onto a surface;
- b) exposing the first layer imagewise to actinic radiation to form a first exposed imaged cross-section, wherein the radiation is of sufficient intensity and duration to cause at least partial curing (e.g., at least 50% curing, as measured by the % conversion of the polymerizable ethylenically unsaturated functional groups initially present in the curable composition) of the layer in the exposed areas;
- c) coating an additional layer of the curable composition onto the previously exposed imaged cross-section;
- d) exposing the additional layer imagewise to actinic radiation to form an additional imaged cross-section, wherein the radiation is of sufficient intensity and duration to cause at least partial curing (e.g., at least 50% curing, as measured by the % conversion of the polymerizable ethylenically unsaturated functional groups initially present in the curable composition) of the additional layer in the exposed areas and to cause adhesion of the additional layer to the previously exposed imaged cross-section;
- e) repeating steps c) and d) a desired number of times to build up the three-dimensional article.
- a) providing a carrier and an optically transparent member having a build surface, the carrier and build surface defining a build region there between;
- b) filling the build region with the curable composition;
- c) continuously or intermittently irradiating the build region with actinic radiation to form a cured composition from the curable composition; and
- d) continuously or intermittently advancing the carrier away from the build surface to form the three-dimensional article from the cured composition.
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group, as described elsewhere herein in more detail, may be substituted for a conventional wax or plastic pattern in such an investment casting process. Such articles, which are comprised of a curable composition resulting from curing of the curable composition, have the advantage of being readily fragmented when contacted with a protic liquid medium such as water, alcohol or aqueous alcohol. Thus, the long burn-out times typically associated with the use of conventional investment patterns may be avoided using the present invention.
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group;
- a) coating a first layer of the curable composition onto a surface;
- b) curing the first layer, at least partially, to provide a cured first layer;
- c) coating a second layer of the curable composition onto the cured first layer;
- d) curing the second layer, at least partially, to provide a cured second layer adhered to the cured first layer; and
- e) repeating steps c) and d) a desired number of times to build up the three-dimensional article.
- a) coating a first layer of the curable composition in liquid form onto a surface;
- b) exposing the first layer imagewise to actinic radiation to form a first exposed imaged cross-section, wherein the radiation is of sufficient intensity and duration to cause at least partial curing of the first layer in the exposed area(s);
- c) coating an additional layer of the curable composition in liquid form onto the previously exposed imaged cross-section;
- d) exposing the additional layer imagewise to actinic radiation to form an additional imaged cross-section, wherein the radiation is of sufficient intensity and duration to cause at least partial curing of the additional layer in the exposed area(s) and to cause adhesion of the additional layer to the previously exposed imaged cross-section;
- e) repeating steps c) and d) a desired number of times to build up the three-dimensional article.
- a) providing a carrier and an optically transparent member having a build surface, the carrier and build surface defining a build region there between;
- b) filling the build region with the curable composition;
- c) continuously or intermittently irradiating the build region with actinic radiation to form a cured composition from the curable composition; and
- d) continuously or intermittently advancing the carrier away from the build surface to form the three-dimensional article from the cured composition.
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group;
wherein the curable composition when cured provides a cured composition which is thermoplastic in the absence of a protic liquid medium, fragmentable in a protic liquid medium and comprises ionic crosslinks as a result of incorporation of the ionic species into a polymeric matrix.
- a) printing a precursor article to the three-dimensional article using a first material and, as a support material to the first material, a curable composition comprised of at least one polymerizable ionic species corresponding to Formula (I):
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group;
wherein the curable composition when cured provides a cured composition which is thermoplastic in the absence of a protic liquid medium, fragmentable in a protic liquid medium and comprises ionic crosslinks as a result of incorporation of the ionic species into a polymeric matrix, to obtain a precursor article comprised of at least one region comprised of the first material and at least one region comprised of the curable composition in cured form; and - b) contacting the precursor article with a protic liquid medium under conditions effective to fragment the at least one region comprised of the curable composition in cured form.
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group;
wherein the curable composition comprises less than 10,000 ppm of each of (meth)acrylic anhydride and water and wherein the curable composition when cured provides a cured composition which is thermoplastic in the absence of a protic liquid medium, fragmentable in a protic liquid medium and comprises ionic crosslinks as a result of incorporation of the ionic species into a polymeric matrix.
A+B− (I)
wherein A+ is a cationic species comprising a cationic functional group and a first polymerizable, ethylenically unsaturated functional group; and B− is an anionic species comprising an anionic functional group and a second polymerizable, ethylenically unsaturated functional group which is the same as or different from the first polymerizable, ethylenically unsaturated functional group;
wherein the curable composition comprises less than 10,000 ppm of each of (meth)acrylic anhydride and water and wherein the curable composition when cured provides a cured composition which is thermoplastic in the absence of a protic liquid medium, fragmentable in a protic liquid medium and comprises ionic crosslinks as a result of incorporation of the ionic species into a polymeric matrix.
Claims (21)
A+B− (I)
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TWI791844B (en) | 2023-02-11 |
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US20210268723A1 (en) | 2021-09-02 |
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